Moneymakers

How Sam Parr Went from Selling Hotdogs to Running The Hustle

Before Sam Parr became a world-class media company founder, he was a sunburnt Nashville hotdog vendor.

2021 saw Americans start 5.4 million new companies, a 20% increase not just from pre-pandemic times, but from any previously recorded year. At Worklife, we love to see people decide to finally go for it and start their own thing. We also love the stories of repeat builders who have been operating for years and can’t get enough of building something from the ground up. Sam Parr (The Hustle founder) is a stand out in this group. 

Sam currently co-runs the My First Million podcast with Shaan Puri. Before that he founded The Hustle (a media company acquired by HubSpot in 2021), and way before that he ran a hot dog business and sold moonshine online.

In August of 2021, I got to sit down as a guest on Shaan Puri and Sam Parr’s podcast. A couple months later, we brought it full circle by inviting Sam onto the Shake Up to chat with me and comedian Alexis Gay about his early career.

Building is rarely a linear path and Sam’s trajectory is no exception:

  • Sam Parr started out as a music business major before ditching college for tech
  • He was an early hire at Air Bed and Breakfast (yep, today’s AirBnB)
  • Sam turned a small meet up into a conference pulling in over a quarter million in revenue
  • He built a high-earning media company all from an email list

Read the full story here or catch it on our podcast. First up: Southern Sam’s Hot Dog Stand.

Sam Parr’s Hot Dog Hustle

Brianne Kimmel: So how did you decide to start a hotdog truck? 

Sam Parr: Hot dog stand! The reason why it’s important that it's not a truck is because there's different laws. And so the barrier to entry for the stand is very low. I was able to get one for 500 bucks and ran it as a side hustle while going to school. 

I don't know how to cook. I still don't. But  I just lucked into it. And I had a funny shtick where it was called “Southern Sam’s, Wieners as big as a baby's arm.” And if you put your baby's arm in a bun, put mustard on it, and let us take a picture of it, then you got a free hot dog.

Alexis Gay: Brilliant. I was listening to your show earlier today and something that really stuck out to me that I feel sets you apart in how you talk about business is that you have a lot of true hands-on real-world experience. 

You really ran a hot dog stand. That's where you started. 

Sam Parr: It was great: 

  • On a slow day, I’d make 200 bucks
  • On a really good day, I’d walk home with $1,000, $2,000 of cash in my pocket 

When you're 21 years old, you're rich. It was a lot of fun. 

It's so hard though. It's just physically demanding. You see my skin. I'm very white and I would get the worst sunburn. It was so hot.

When I was doing it, I was like, “I need to make money on the internet.”

I started an online store and I would be in class and my phone would be going ka-ching, ka-ching. And I would walk out of class with a thousand dollars in my PayPal account. And I'm like, “oh man, this is way better.”

Alexis Gay: What was that business? 

Sam Parr: So it was an online liquor store. But eventually I got rid of that and I got rid of the hotdog stand and I moved out to San Francisco.

Sam Parr Starts Up in Tech

Brianne Kimmel: How did you make the jump from hotdogs to tech?

Sam Parr: I cold emailed this guy named Brian. And he had a company called Air Bed and Breakfast. I was like, “Hey, this sounds like a cool thing. I want to interview. I think I can help make it better by doing X, Y, and Z.” And they were like, “Are you in the Bay Area?” And I was like, “Yeah, yeah, yeah, I'm there.” And he goes, “Alright, great. Come to the office on Monday.”

So I booked the flight and I flew out and got an interview there.

That's how I got introduced to startups. And then I eventually got rid of all my stuff and moved to San Francisco. 

Alexis Gay: How did you identify that Air Bed and Breakfast was a startup you really saw potential in to the point that you were willing to move your entire life?

Sam Parr: I don't know. I didn’t really think too far ahead of what was going to happen. When I was talking and telling my parents about it they're like, “this sounds like a Ponzi scheme.”

So how did I know that they were going to be interesting? I didn't. I had no idea. It was a total guess. It sounded cool.

One of their fifth or eighth employees, something like that, was a guy named Chris Lukezik and he was a famous runner. I was a runner. I went to school on an athletic scholarship for track and field. 

Lukezic quit his professional career as a runner—which isn't exactly lucrative—to work as the eighth employee or something at Air Bed and Breakfast. And I was like, “Damn, if this guy went to Georgetown, he's probably smart.” And he quit his running career. I'm in. And so that's how I got looped.

Sam Parr Hustles for Hustle Con

Brianne Kimmel: This a great segue to looking at tech and startup culture. I'd love to spend some time and learn about what was that initial inflection point or that initial idea that led to the Hustle.

Sam Parr: So I basically launched this thing called Hustle Con. I created the website and I announced it.

I didn't have many people to announce it to, but I announced it on June 1st. And I think it happened on July 15th. 

It made like 60 grand in profit. I thought it totally wasn't going to work. I thought maybe I would just kill some time and meet someone to start something with and it worked.

And then I did it again. And this time it made a quarter of a million dollars in profit. 

Alexis Gay: Whoa, wait. So are you saying this predates the newsletter and the show?

Sam Parr: Yeah, I started that in 2015—or maybe 14 and 15. I would host an event, get money, and ride my motorcycle around the country.

Alexis Gay: Was it just you building it? It's just you on a computer and a motorcycle at this point? 

Sam Parr: With Hustle Con, yeah, I was the only employee. I had a team of volunteers. When people showed up to the event, they would hand them bottled water, things like that.

Brianne Kimmel: It's interesting because to have volunteers means that there was a community and there were people that were really rallying behind what you were doing. What types of people were these and what got them so excited about Hustle Con?

Sam Parr: It was non-technical founders.

We had Katrina Lake. She started Stitch Fix. And we had her right when she had raised her seed round I believe. And then we had Jess Lee, the woman who started Polyvore. 

A lot of companies that are quite big now, we would have them come and speak at our event.

And Jess wasn't technical. Katrina talked about how she built Stitch Fix using an Excel model. Stitch Fix is like, what, a $3 billion company? And so it was all about people who founded tech companies, but they didn't know how to code. And so that was the original niche. 

Alexis Gay: Why was that the original niche that you picked?

Sam Parr: I didn't pick it. I knew someone who had hosted this event as a meetup before, and I met these guys and I was like, “Hey, I don't have anything to do. Can I take this over?” And their thing was pretty small, but they let me take it over. And I just gave them a small cut of the profit. 

The way that I got the people to buy tickets was I created a newsletter and I would write about the speakers in a fun way.

April 19th, 2016, The Hustle launched as an email.

I had this blog prior to that where I was able to get millions of people to come to the website. A fair amount of people would give me their email. Then I would write more and send my articles to them and then they would share some more and I would get all this traffic. 

Eventually, I read about this company called DailyCandy—a newsletter company.

I decided I should do an email instead of blogging. I wanted to create this daily email that reached millions of people for the business and tech world. I wanted to:

  • Make profits through advertising
  • Use those profits to invest in cool companies 
  • Tell my audience about the cool companies that we invested in

I thought that it would create this interesting cycle. 

We ended up selling before we got to the third part of investing in companies, but we made a lot of profit through ads and we built a big audience. 

The Hustle, Sam Parr’s Media Company

Alexis Gay: I want to hear a little bit more about the media company itself. You were building a brand online. Was there a moment when you realized, oh, I'm building a media company? 

Sam Parr: Look, I'm a content producer. So I'm a writer. I wouldn't call myself a journalist, I would call myself a blogger, and I had always done it. And eventually we got a hundred thousand or 200,000 email subscribers in our first year. We were able to get there through blogging. 

  • It took about nine months to get ad revenue
  • The second year, I think we did 2.2 million
  • The third year, maybe five million
  • Then around seven million
  • Then 13 million
  • This year I think we could have done 20 million

And so it probably wasn't until year two when we were making $2 million that I thought “This could maybe actually become a legitimate thing.”

Sam Parr’s Favorites and Forecasts 

Alexis Gay: How do you see media companies making money moving forward?

Sam Parr: I think the subscription business is wonderful. So when the Hustle got acquired we were doing a lot of revenue and advertising. Advertising can make you a lot of money. I don't like it, but there's a lot of things I don't like and that doesn't mean it's not good. And then we had millions of dollars in subscription revenue, and that was awesome.

I love subscription revenue. I think a lot of people don't do it because they're too fearful. Typically, if you have an ad business, that is the opposite of what's necessary for a subscription. So like your writers, are they going to be incentivized to go for reach or to go for keep? It’s really hard to have both, but I think more should have subscriptions.

In general, media is hard, man. Once HubSpot bought us and I started seeing some of the numbers and I started learning about enterprise software. I'm like, “This is way better.”

Brianne Kimmel: What do you think about media companies selling merch?

Sam Parr: I think it will only work for a few people. If you’re Barstool that will work. If you're the Chive that will work. It's very hard to make a lot of money that way, I think. 

Brianne Kimmel: Which independent media company do you admire the most today?

Sam Parr: Reddit isn't a media company exactly, but I think that what Reddit is doing, it's just the greatest thing on earth. I think the nerd culture is amazing. There's a niche community for everything. 

Like my wife was complaining for years—so my wife is Black—because there was an issue with her hair. And I couldn't help her, but I went on Reddit and I'm like, “Hey, look, there's 50,000 people who are part of the subreddit”—I think it's called “Black Curly Hair” or something like that—“There's your answer. We just found it.” And so now she's an active part of this community and she got the answer and I think that's amazing. You can't find that anywhere else. 

Alexis Gay: What stands out to you as the most exciting next big thing that you could really sink your teeth into?]

Sam Parr: This’ll be a little bit of a weird one, but trucking in America. 

The American trucker, I think, has been shit on for like the past couple of decades. Wages are at an all time low. It's an incredibly hard job. But, without trucks, we don't get the food that we want. You don't get that microphone. You don't get this, you don't get that. You have to have trucks. And I've always been fascinated about these problems of Middle America—”normal people”—which I identify as and I think of as my roots. 

How do we make their lives a little bit better? The trucking union is one of the most powerful unions. I think I might explore that.

Builders and Side Hustles Will Continue to Thrive

As Gen Z enters the workplace and the Great Resignation continues, employers and builders will have to adapt quickly to keep up with workers’ changing job requirements. 

Like Sam forecasts, this collective reimagining of work will touch the lives of people across the economy, from founders to office workers to truckers. 

Whether someone is working full time or running multiple hustles, we’re living in an age where building something new from the ground up is within reach. 

Sam’s career trajectory is a great example of the new American dream: work that is flexible, creative, and self-designed. At Worklife, we’re excited to see this trend continue to grow. ∎

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